Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

More Documents

117706

Sigma-Aldrich

Phenylacetylene

98%

Synonym(s):

Ethynylbenzene

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
C6H5CCH
CAS Number:
536-74-3
Molecular Weight:
102.13
Beilstein/REAXYS Number:
605461
MDL number:
MFCD00008570
UNSPSC Code:
12352100
PubChem Substance ID:
24847341
NACRES:
NA.22

vapor pressure

17.6 mmHg ( 37.7 °C)

assay

98%

impurities

<1% 1,4-dioxane

refractive index

n20/D 1.549 (lit.)

bp

142-144 °C (lit.)

solubility

H2O: insoluble
alcohol: miscible
diethyl ether: miscible

density

0.93 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C#Cc1ccccc1

InChI

1S/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H

InChI key

UEXCJVNBTNXOEH-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

Phenylacetylene is an aromatic organic compound frequently employed in Sonogashira coupling reactions. Phenylacetylene undergoes polymerization catalyzed by Rh and Pt complexes to form polyphenylacetylene.

Application

Phenylacetylene was used in a study to investigate the mechanism of product formation during the palladium-catalysed phenylacetylene oxidative carbonylation reaction.
Terminal acetylene used in the conversion of nitrones to alkynyl hydroxyl amines in the presence of trimethylaluminum..

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Carc. 1B - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

80.6 °F - closed cup

flash_point_c

27 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Katarina Novakovic et al.
Physical chemistry chemical physics : PCCP, 10(5), 749-753 (2008-02-07)
This paper reports on the influence of oscillations on product selectivity as well as the dynamics of product formation during the palladium-catalysed phenylacetylene oxidative carbonylation reaction in a catalytic system (PdI2, KI, Air, NaOAc in methanol). The occurrence of the
Rhodium and platinum complexes as catalysts for the polymerization of phenylacetylene.
Furlani A, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 24(5), 991-1005 (1986)
Tetrahedron Letters, 48, 1457-1457 (2007)
Kyoung Chul Ko et al.
The journal of physical chemistry. A, 116(25), 6837-6844 (2012-06-06)
The intramolecular magnetic coupling constant (J) values of diradical systems linked with two monoradicals through a coupler (para-substituted phenyl acetylene (Model I), meta-substituted phenyl acetylene (Model II), ethylene (Model III)) were investigated by unrestricted density functional theory calculations. We divided
Zhouqing Xu et al.
Chemical communications (Cambridge, England), 48(46), 5736-5738 (2012-05-09)
[8+12]-metallamacrocycle-based 3D frameworks {[Cu(4)(pbt)(2)(SO(4))(2)(DMF)(2)(CH(3)OH)]·7H(2)O·DMF}(n) (1) and [12]-macrocycle 3D {[Cu(2)(pbt)(SO(4))(DMSO)(CH(3)OH)(2)]·5H(2)O·CH(3)OH}(n) (2) have been obtained. Both complexes display antiferromagnetic couplings and high catalytic activity in the oxidative coupling reaction of 1-ethynylbenzene and oxazolidin-2-one.
View All Related Papers

Articles

New Aromatic Terminal Alkynes

The terminal alkyne functionality has a wide range of applications including most recently the synthesis of spiropyran substituted 2,3-dicyanopyrazines and (±)-asteriscanolide, as well as conversion to enamines using resin-bound 2° amines.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service